Food Lipids: Chemistry, Nutrition, and Biotechnology

Figure 11 Microbial production of dicarboxylic acids.
5. Ketones and Lactones
Fatty acids and their esters (triacylglycerols) have been converted to methylalkylketones
having an alkyl chain one carbon shorter than the substrate using filamentous
fungus Penicillium roquefortii (89) and the fungus Trichoderma sp. (90). A black
yeast, Aureobasidium sp., produces from lauric acid–rich palm kernel oil n-undecane-2-one
and n-undecane-2-ol in good yields (91). A fungus, Fusarium avenaceum
sp., produces monohydroxy-n-nonane-2-ones from tricaprin (92). These reactions are
outlined in Fig. 12.
The fungi Mucor javanicus and Mucor miehei catalyze the lactonization of �hydroxy
fatty acids, e.g., 15-hydroxypentadecanoic and 16-hydroxyhexadecanoic
acids, to the corresponding macrocyclic mono- and oligolactones (93) as shown in
Fig. 13.
10-Hydroxystearic acid, prepared by microbial oxidation of oleic acid, has been
converted to �-dodecalactone by baker’s yeast, possibly via � oxidation (94).
III. MODIFICATION OF FATS AND OTHER LIPIDS USING
ISOLATED ENZYMES
Enzymes of lipid metabolism, isolated from microorganisms, plants, and animal tissues,
are highly suitable for biotransformation of fats and other lipids because many
of these enzymatic reactions do not require cofactors, and a large number of such
enzyme preparations are commercially available. This section will cover the applications
of lipolytic enzymes, such as triacylglycerol lipases and phospholipases, as
well as the use of oxygenases, lipoxygenases, and epoxide hydrolases in the biomodification
of fats and other lipids.
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